NCO-free compounds and usage thereof in a curable composition

Patent metadata

Field	Value
Publication number	US-10577463-B2
Application number	US-201715472523-A
Country	US
Kind code	B2
Filing date	Mar 29, 2017
Priority date	Sep 30, 2014
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

The invention relates to a compound comprising at least two —(NH—C═O)— groups and at least two —(C═O)—C≡C—R1 groups, wherein R1 represents hydrogen or a group having from 1 to 12 carbon atoms; a curable composition comprising a first unit comprising at least two —(NH—C═O)— groups, a second unit comprising at least two —(C═O)—C≡C—R1 groups, and a catalyst; and the use of the composition as an adhesive, coating, casting composition or as sealant.

First claim

The invention claimed is:

1. A compound comprising at least two —(NH—C═O)— groups and at least two —(C═O)—C≡C—R 1 groups,
wherein the —(NH—C═O)— groups are provided by urea and/or urethane groups and R 1 represents hydrogen or a group having from 1 to 12 carbon atoms.

2. The compound according to claim 1 , wherein the —(NH—C═O)— groups are provided by urethane groups.

3. The compound according to claim 1 , obtained by
a) reacting a polyisocyanate with at least two isocyanate groups with a polyol or a polyamine or a mixture thereof to form an intermediate,
wherein the molar ratio of the NCO groups of the polyisocyanate to the sum of hydroxyl groups, primary amino groups and secondary amino groups of the polyol and polyamine is less than 1; and

b) reacting a compound of the formula R 2 O—(C═O)—C≡C—R 1 with the intermediate of step a) in molar excess to the sum of hydroxyl groups, primary amino groups and secondary amino groups of the intermediate,
wherein R 1 represents hydrogen or a group having from 1 to 12 carbon atoms, and R 2 represents hydrogen or a group having from 1 to 4 carbon atoms.

4. The compound according to claim 3 , wherein the polyol is selected from a group comprising polyether polyols, polyether polyol block-copolymers, polyester polyols, polyester polyol block-copolymers or mixtures thereof and mixtures thereof.

5. The compound according to claim 3 , wherein the polyol is selected from a group comprising polyethylene glycol, polypropylene glycol and polytetrahydrofuran, and mixtures thereof.

6. The compound according to claim 3 , wherein the number average molar weight (M n ) of the polyol/polyamine from 1000 to 5000 g/mol.

7. The compound according to claim 3 , wherein the polyisocyanate is selected from a group comprising 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 2,2′-diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, 4,4′-methylene dicyclohexyl diisocyanate, 2,4′-methylene dicyclohexyl diisocyanate, 2,2′-methylene dicyclohexyl diisocyanate, and mixtures thereof.

8. A compound comprising at least two —(NH—C═O)— groups and at least two —(C═O)—C≡C—R 1 groups, wherein R 1 represents hydrogen or CH 3 .

9. A curable composition comprising:
a first unit comprising at least two —(NH—C═O)— groups,
a second unit comprising at least two —(C═O)—C≡C—R 1 groups, and
a catalyst,
wherein R 1 represents hydrogen or a group having 1 to 12 carbon atoms.

10. The curable composition according to claim 9 , wherein the —(NH—C═O)— groups are provided by urea and/or urethane groups.

11. The curable composition according to claim 9 , wherein the first and the second units are part of one compound.

12. The curable composition according to claim 9 , wherein the first and the second unit are part of different compounds.

13. The curable composition according to claim 9 , wherein the first and the second unit are part of different compounds and the first unit is part of a thermoplastic polyurethane.

14. The curable composition according to claim 9 , wherein the catalyst is a secondary or tertiary amine.

15. The curable composition according to claim 9 , wherein the catalyst is selected from the group consisting of 1,4-diazabicyclo[2.2.2]octane, tetramethylethylenediamine, N,N-diisopropylethylamine, triethanolamine, tris(2-pyridylmethyl)amine, tributylamine, 4-dimethylaminophenol, N-ethyl-N-methyl propylamine, N-methyl piperidine, N-butyl-4-hydroxy piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, imidazoline, benzimidazole, dimethylamino ethanol, pirrole, morpholine, piperidine, piperazine, indole, and mixtures thereof.

16. The curable composition according to claim 9 , wherein the catalyst is 1,4-diazabicyclo[2.2.2]octane.

17. The curable composition according to claim 9 , wherein the second unit is provided by a compound that is the reaction product of a polyether polyol with at least two OH groups with a compound of the formula R 2 O—(C═O)—C≡C—R 1 in a quantity at least equivalent to two OH groups of the polyether polyol,
wherein R 1 represents hydrogen or a group having 1 to 12 carbon atoms, and
R 2 represents hydrogen or a group having 1 to 4 carbon atoms.

18. The curable composition according to claim 17 , wherein the number average molar mass (M n ) of the compound comprising the second unit is from 500 to 1500 g/mol.

19. An adhesive, coating, casting composition or sealant comprising the composition of claim 9 .

Assignees

• Henkel Ag & Co Kgaa
• Henkel IP & Holding GmbH

Inventors

• Zhao Ligang
• Pela Roberto
• Dai Weifeng
• Mcardle Ciaran
• Alcazar Eva Maria
• Bertomeu Maria Merce
• Bongartz Nils
• Liu Jun

Classifications

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C09J175/02

  Polyureas · CPC title

• C08L75/08

  from polyethers · CPC title

• C08G71/04 Primary

  Polyurethanes · CPC title